(E)-2-[4-(Dimethyl-amino)-styr-yl]-1-methyl-pyridinium 4-methyl-benzene-sulfonate monohydrate.

The cation of the title compound, C(16)H(19)N(2) (+)·C(7)H(7)O(3)S(-)·H(2)O, exists in the E configuration with respect to the C=C double bond and is essentially planar, the dihedral angle between the pyridinium and benzene rings being 3.55 (13)°. In the crystal, π-conjugated planes of cations and anions are inclined to each other at 84.30 (11)°. The crystal structure is stabilized by O-H⋯O hydrogen bonds and weak C-H⋯O inter-actions, which link the cations, anions and water mol-ecules into chains along the b axis. These chains are stacked along the a axis by π-π inter-actions with centroid-centroid distances of 3.6032 (16) and 3.6462 (16) Å.

Related literature

For bond-length data, see Allen et al. (1987 ▶). For background to and applications of quarternary ammonium compounds and sulfonamides, see: Barlow et al. (1937 ▶); Ohkura et al. (2003 ▶); Pernak et al. (2001 ▶). For related structures, see: Chanawanno et al. (2010 ▶); Kobkeatthawin et al. (2009 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C16H19N2 +·C7H7O3S−·H2O

M = 428.53

Triclinic,

a = 7.3469 (9) Å

b = 9.8860 (12) Å

c = 15.5541 (19) Å

α = 75.801 (3)°

β = 79.438 (3)°

γ = 76.865 (2)°

V = 1056.8 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.19 mm−1

T = 100 K

0.47 × 0.13 × 0.06 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.919, T max = 0.989

15705 measured reflections

4122 independent reflections

3307 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.156

S = 1.11

4122 reflections

282 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.51 e Å−3

Δρmin = −0.56 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810026309/sj5034sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810026309/sj5034Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C16H19N2+·C7H7O3S−·H2O	Z = 2
Mr = 428.53	F(000) = 456
Triclinic, P1	Dx = 1.347 Mg m−3
Hall symbol: -P 1	Melting point = 468–469 K
a = 7.3469 (9) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.8860 (12) Å	Cell parameters from 4122 reflections
c = 15.5541 (19) Å	θ = 1.4–26.0°
α = 75.801 (3)°	µ = 0.19 mm−1
β = 79.438 (3)°	T = 100 K
γ = 76.865 (2)°	Needle, orange
V = 1056.8 (2) Å3	0.47 × 0.13 × 0.06 mm

Bruker APEXII DUO CCD area-detector diffractometer	4122 independent reflections
Radiation source: sealed tube	3307 reflections with I > 2σ(I)
graphite	Rint = 0.045
φ and ω scans	θmax = 26.0°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −9→9
Tmin = 0.919, Tmax = 0.989	k = −12→12
15705 measured reflections	l = −19→19

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.156	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ2(Fo2) + (0.069P)2 + 1.5338P] where P = (Fo2 + 2Fc2)/3
4122 reflections	(Δ/σ)max = 0.001
282 parameters	Δρmax = 0.51 e Å−3
0 restraints	Δρmin = −0.56 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
N1	1.0171 (3)	0.9737 (2)	0.12371 (15)	0.0145 (5)
N2	−0.1299 (3)	0.8266 (3)	0.39380 (16)	0.0215 (5)
C1	1.1969 (4)	0.9572 (3)	0.08076 (18)	0.0176 (6)
H1A	1.2683	1.0256	0.0766	0.021*
C2	1.2745 (4)	0.8414 (3)	0.04353 (19)	0.0198 (6)
H2A	1.3976	0.8309	0.0143	0.024*
C3	1.1662 (4)	0.7399 (3)	0.05011 (18)	0.0189 (6)
H3A	1.2161	0.6606	0.0252	0.023*
C4	0.9842 (4)	0.7579 (3)	0.09382 (18)	0.0170 (6)
H4A	0.9115	0.6905	0.0975	0.020*
C5	0.9067 (4)	0.8750 (3)	0.13271 (18)	0.0152 (5)
C6	0.7180 (4)	0.8965 (3)	0.18253 (18)	0.0166 (6)
H6A	0.6710	0.9821	0.2007	0.020*
C7	0.6089 (4)	0.7978 (3)	0.20334 (18)	0.0177 (6)
H7A	0.6566	0.7156	0.1812	0.021*
C8	0.4235 (4)	0.8062 (3)	0.25704 (18)	0.0166 (5)
C9	0.3246 (4)	0.6955 (3)	0.26819 (19)	0.0182 (6)
H9A	0.3816	0.6174	0.2431	0.022*
C10	0.1460 (4)	0.6991 (3)	0.31509 (18)	0.0168 (6)
H10A	0.0860	0.6230	0.3223	0.020*
C11	0.0532 (4)	0.8173 (3)	0.35233 (18)	0.0163 (5)
C12	0.1546 (4)	0.9257 (3)	0.34420 (18)	0.0176 (6)
H12A	0.0992	1.0026	0.3707	0.021*
C13	0.3347 (4)	0.9203 (3)	0.29778 (18)	0.0172 (6)
H13A	0.3980	0.9937	0.2935	0.021*
C14	0.9449 (4)	1.1036 (3)	0.16027 (19)	0.0186 (6)
H14A	0.8340	1.1563	0.1345	0.028*
H14B	1.0398	1.1612	0.1460	0.028*
H14C	0.9142	1.0774	0.2241	0.028*
C15	−0.2224 (4)	0.7057 (3)	0.4121 (2)	0.0236 (6)
H15A	−0.2238	0.6787	0.3570	0.035*
H15B	−0.3496	0.7309	0.4400	0.035*
H15C	−0.1552	0.6275	0.4515	0.035*
C16	−0.2284 (4)	0.9532 (3)	0.4263 (2)	0.0248 (6)
H16A	−0.2241	1.0353	0.3784	0.037*
H16B	−0.1688	0.9626	0.4740	0.037*
H16C	−0.3574	0.9455	0.4481	0.037*
S1	0.39079 (9)	0.30482 (7)	0.18364 (5)	0.01550 (19)
O1	0.3624 (3)	0.2330 (2)	0.11664 (13)	0.0202 (4)
O2	0.4315 (3)	0.4458 (2)	0.14332 (13)	0.0214 (5)
O3	0.5235 (3)	0.2178 (2)	0.24342 (14)	0.0205 (4)
C17	0.1685 (3)	0.3327 (3)	0.25164 (18)	0.0138 (5)
C18	0.0064 (4)	0.3932 (3)	0.21068 (18)	0.0157 (5)
H18A	0.0153	0.4239	0.1488	0.019*
C19	−0.1682 (4)	0.4069 (3)	0.26349 (19)	0.0170 (6)
H19A	−0.2767	0.4449	0.2364	0.020*
C20	−0.1835 (4)	0.3651 (3)	0.35578 (19)	0.0182 (6)
C21	−0.0197 (4)	0.3085 (3)	0.39579 (19)	0.0196 (6)
H21A	−0.0280	0.2819	0.4578	0.024*
C22	0.1561 (4)	0.2916 (3)	0.34368 (18)	0.0166 (6)
H22A	0.2647	0.2529	0.3707	0.020*
C23	−0.3743 (4)	0.3757 (3)	0.4126 (2)	0.0266 (7)
H23A	−0.3581	0.3418	0.4746	0.040*
H23B	−0.4472	0.3190	0.3963	0.040*
H23C	−0.4389	0.4730	0.4031	0.040*
O1W	0.7344 (3)	0.5643 (2)	0.04598 (15)	0.0251 (5)
H1W1	0.645 (7)	0.524 (5)	0.070 (3)	0.056 (13)*
H2W1	0.699 (5)	0.618 (4)	−0.009 (3)	0.033 (10)*

	U11	U22	U33	U12	U13	U23
N1	0.0088 (10)	0.0153 (11)	0.0197 (11)	−0.0024 (9)	−0.0005 (9)	−0.0051 (9)
N2	0.0114 (12)	0.0250 (13)	0.0286 (13)	−0.0059 (10)	0.0045 (10)	−0.0096 (10)
C1	0.0078 (12)	0.0207 (14)	0.0230 (14)	−0.0019 (10)	−0.0013 (10)	−0.0038 (11)
C2	0.0083 (13)	0.0234 (14)	0.0237 (14)	0.0021 (11)	0.0016 (11)	−0.0049 (11)
C3	0.0164 (14)	0.0163 (13)	0.0209 (14)	0.0024 (11)	−0.0021 (11)	−0.0034 (11)
C4	0.0140 (13)	0.0148 (13)	0.0213 (14)	−0.0014 (10)	−0.0025 (11)	−0.0032 (11)
C5	0.0115 (13)	0.0154 (13)	0.0180 (13)	−0.0019 (10)	−0.0030 (10)	−0.0019 (10)
C6	0.0109 (13)	0.0168 (13)	0.0203 (14)	−0.0003 (10)	−0.0005 (10)	−0.0040 (11)
C7	0.0113 (13)	0.0174 (13)	0.0231 (14)	−0.0003 (10)	−0.0018 (11)	−0.0046 (11)
C8	0.0105 (13)	0.0167 (13)	0.0211 (14)	−0.0016 (10)	−0.0023 (10)	−0.0022 (10)
C9	0.0136 (14)	0.0154 (13)	0.0251 (14)	−0.0002 (11)	−0.0034 (11)	−0.0050 (11)
C10	0.0129 (13)	0.0149 (13)	0.0239 (14)	−0.0069 (10)	−0.0024 (11)	−0.0026 (11)
C11	0.0102 (13)	0.0192 (13)	0.0179 (13)	−0.0028 (10)	−0.0011 (10)	−0.0018 (10)
C12	0.0149 (13)	0.0166 (13)	0.0213 (14)	−0.0028 (11)	−0.0015 (11)	−0.0052 (11)
C13	0.0117 (13)	0.0175 (13)	0.0221 (14)	−0.0035 (10)	−0.0024 (11)	−0.0028 (11)
C14	0.0114 (13)	0.0176 (13)	0.0275 (15)	−0.0020 (10)	0.0016 (11)	−0.0100 (11)
C15	0.0147 (14)	0.0294 (16)	0.0268 (15)	−0.0090 (12)	0.0022 (12)	−0.0054 (12)
C16	0.0145 (14)	0.0289 (16)	0.0283 (16)	−0.0032 (12)	0.0053 (12)	−0.0082 (13)
S1	0.0063 (3)	0.0145 (3)	0.0248 (4)	−0.0030 (2)	0.0034 (2)	−0.0058 (3)
O1	0.0130 (10)	0.0195 (10)	0.0287 (11)	−0.0047 (8)	0.0046 (8)	−0.0104 (8)
O2	0.0116 (10)	0.0181 (10)	0.0320 (11)	−0.0049 (8)	0.0060 (8)	−0.0052 (8)
O3	0.0055 (9)	0.0211 (10)	0.0332 (11)	0.0004 (7)	−0.0020 (8)	−0.0057 (8)
C17	0.0055 (12)	0.0123 (12)	0.0236 (14)	−0.0031 (9)	0.0029 (10)	−0.0064 (10)
C18	0.0112 (13)	0.0150 (13)	0.0210 (14)	−0.0029 (10)	−0.0015 (10)	−0.0040 (10)
C19	0.0086 (12)	0.0130 (13)	0.0296 (15)	0.0001 (10)	−0.0039 (11)	−0.0059 (11)
C20	0.0087 (13)	0.0195 (13)	0.0269 (15)	−0.0050 (10)	0.0044 (11)	−0.0086 (11)
C21	0.0153 (14)	0.0233 (14)	0.0196 (14)	−0.0052 (11)	0.0006 (11)	−0.0043 (11)
C22	0.0091 (13)	0.0171 (13)	0.0244 (14)	−0.0032 (10)	−0.0028 (10)	−0.0049 (11)
C23	0.0117 (14)	0.0357 (17)	0.0310 (16)	−0.0056 (12)	0.0055 (12)	−0.0098 (13)
O1W	0.0169 (11)	0.0311 (12)	0.0287 (12)	−0.0126 (9)	0.0002 (9)	−0.0038 (10)

N1—C1	1.360 (3)	C14—H14A	0.9600
N1—C5	1.372 (3)	C14—H14B	0.9600
N1—C14	1.480 (3)	C14—H14C	0.9600
N2—C11	1.374 (3)	C15—H15A	0.9600
N2—C15	1.450 (4)	C15—H15B	0.9600
N2—C16	1.454 (4)	C15—H15C	0.9600
C1—C2	1.371 (4)	C16—H16A	0.9600
C1—H1A	0.9300	C16—H16B	0.9600
C2—C3	1.390 (4)	C16—H16C	0.9600
C2—H2A	0.9300	S1—O3	1.454 (2)
C3—C4	1.378 (4)	S1—O2	1.4553 (19)
C3—H3A	0.9300	S1—O1	1.464 (2)
C4—C5	1.396 (4)	S1—C17	1.780 (3)
C4—H4A	0.9300	C17—C22	1.381 (4)
C5—C6	1.456 (4)	C17—C18	1.396 (4)
C6—C7	1.343 (4)	C18—C19	1.389 (4)
C6—H6A	0.9300	C18—H18A	0.9300
C7—C8	1.458 (4)	C19—C20	1.384 (4)
C7—H7A	0.9300	C19—H19A	0.9300
C8—C13	1.402 (4)	C20—C21	1.395 (4)
C8—C9	1.406 (4)	C20—C23	1.511 (4)
C9—C10	1.377 (4)	C21—C22	1.392 (4)
C9—H9A	0.9300	C21—H21A	0.9300
C10—C11	1.411 (4)	C22—H22A	0.9300
C10—H10A	0.9300	C23—H23A	0.9600
C11—C12	1.407 (4)	C23—H23B	0.9600
C12—C13	1.383 (4)	C23—H23C	0.9600
C12—H12A	0.9300	O1W—H1W1	0.83 (5)
C13—H13A	0.9300	O1W—H2W1	0.94 (4)
C1—N1—C5	121.8 (2)	H14A—C14—H14B	109.5
C1—N1—C14	117.0 (2)	N1—C14—H14C	109.5
C5—N1—C14	121.2 (2)	H14A—C14—H14C	109.5
C11—N2—C15	120.3 (2)	H14B—C14—H14C	109.5
C11—N2—C16	120.6 (2)	N2—C15—H15A	109.5
C15—N2—C16	118.9 (2)	N2—C15—H15B	109.5
N1—C1—C2	121.1 (2)	H15A—C15—H15B	109.5
N1—C1—H1A	119.5	N2—C15—H15C	109.5
C2—C1—H1A	119.5	H15A—C15—H15C	109.5
C1—C2—C3	118.9 (2)	H15B—C15—H15C	109.5
C1—C2—H2A	120.5	N2—C16—H16A	109.5
C3—C2—H2A	120.5	N2—C16—H16B	109.5
C4—C3—C2	119.4 (2)	H16A—C16—H16B	109.5
C4—C3—H3A	120.3	N2—C16—H16C	109.5
C2—C3—H3A	120.3	H16A—C16—H16C	109.5
C3—C4—C5	121.5 (2)	H16B—C16—H16C	109.5
C3—C4—H4A	119.3	O3—S1—O2	113.73 (11)
C5—C4—H4A	119.3	O3—S1—O1	113.30 (12)
N1—C5—C4	117.3 (2)	O2—S1—O1	111.86 (12)
N1—C5—C6	118.9 (2)	O3—S1—C17	106.05 (12)
C4—C5—C6	123.8 (2)	O2—S1—C17	105.69 (11)
C7—C6—C5	122.8 (2)	O1—S1—C17	105.35 (11)
C7—C6—H6A	118.6	C22—C17—C18	120.5 (2)
C5—C6—H6A	118.6	C22—C17—S1	120.3 (2)
C6—C7—C8	126.8 (3)	C18—C17—S1	119.2 (2)
C6—C7—H7A	116.6	C19—C18—C17	119.1 (2)
C8—C7—H7A	116.6	C19—C18—H18A	120.4
C13—C8—C9	117.2 (2)	C17—C18—H18A	120.4
C13—C8—C7	123.7 (2)	C20—C19—C18	121.2 (2)
C9—C8—C7	119.0 (2)	C20—C19—H19A	119.4
C10—C9—C8	122.1 (2)	C18—C19—H19A	119.4
C10—C9—H9A	119.0	C19—C20—C21	118.9 (2)
C8—C9—H9A	119.0	C19—C20—C23	120.9 (3)
C9—C10—C11	120.6 (2)	C21—C20—C23	120.2 (3)
C9—C10—H10A	119.7	C22—C21—C20	120.6 (3)
C11—C10—H10A	119.7	C22—C21—H21A	119.7
N2—C11—C12	121.5 (2)	C20—C21—H21A	119.7
N2—C11—C10	121.1 (2)	C17—C22—C21	119.6 (2)
C12—C11—C10	117.4 (2)	C17—C22—H22A	120.2
C13—C12—C11	121.5 (2)	C21—C22—H22A	120.2
C13—C12—H12A	119.3	C20—C23—H23A	109.5
C11—C12—H12A	119.3	C20—C23—H23B	109.5
C12—C13—C8	121.1 (2)	H23A—C23—H23B	109.5
C12—C13—H13A	119.5	C20—C23—H23C	109.5
C8—C13—H13A	119.5	H23A—C23—H23C	109.5
N1—C14—H14A	109.5	H23B—C23—H23C	109.5
N1—C14—H14B	109.5	H1W1—O1W—H2W1	105 (4)
C5—N1—C1—C2	0.8 (4)	C9—C10—C11—N2	175.4 (3)
C14—N1—C1—C2	−178.9 (3)	C9—C10—C11—C12	−3.8 (4)
N1—C1—C2—C3	0.1 (4)	N2—C11—C12—C13	−176.0 (3)
C1—C2—C3—C4	−0.1 (4)	C10—C11—C12—C13	3.1 (4)
C2—C3—C4—C5	−0.8 (4)	C11—C12—C13—C8	−0.1 (4)
C1—N1—C5—C4	−1.7 (4)	C9—C8—C13—C12	−2.3 (4)
C14—N1—C5—C4	178.1 (2)	C7—C8—C13—C12	176.7 (3)
C1—N1—C5—C6	177.6 (2)	O3—S1—C17—C22	8.8 (2)
C14—N1—C5—C6	−2.6 (4)	O2—S1—C17—C22	−112.3 (2)
C3—C4—C5—N1	1.7 (4)	O1—S1—C17—C22	129.2 (2)
C3—C4—C5—C6	−177.6 (3)	O3—S1—C17—C18	−169.54 (19)
N1—C5—C6—C7	−172.2 (3)	O2—S1—C17—C18	69.4 (2)
C4—C5—C6—C7	7.1 (4)	O1—S1—C17—C18	−49.1 (2)
C5—C6—C7—C8	176.3 (3)	C22—C17—C18—C19	−2.3 (4)
C6—C7—C8—C13	−2.3 (4)	S1—C17—C18—C19	176.08 (19)
C6—C7—C8—C9	176.7 (3)	C17—C18—C19—C20	1.6 (4)
C13—C8—C9—C10	1.6 (4)	C18—C19—C20—C21	0.1 (4)
C7—C8—C9—C10	−177.4 (3)	C18—C19—C20—C23	−177.9 (2)
C8—C9—C10—C11	1.5 (4)	C19—C20—C21—C22	−1.3 (4)
C15—N2—C11—C12	−171.6 (3)	C23—C20—C21—C22	176.7 (2)
C16—N2—C11—C12	3.5 (4)	C18—C17—C22—C21	1.1 (4)
C15—N2—C11—C10	9.3 (4)	S1—C17—C22—C21	−177.2 (2)
C16—N2—C11—C10	−175.6 (3)	C20—C21—C22—C17	0.7 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···O2	0.83 (5)	1.96 (5)	2.774 (3)	170 (4)
O1W—H2W1···O1i	0.94 (4)	1.99 (4)	2.906 (3)	167 (3)
C1—H1A···O1ii	0.93	2.55	3.424 (3)	157
C2—H2A···O1iii	0.93	2.54	3.382 (4)	150
C4—H4A···O1W	0.93	2.35	3.222 (4)	157
C6—H6A···O3iv	0.93	2.53	3.456 (4)	176
C9—H9A···O2	0.93	2.49	3.376 (3)	158
C13—H13A···O3iv	0.93	2.49	3.390 (4)	164
C14—H14B···O1ii	0.96	2.56	3.479 (4)	161
C22—H22A···O3	0.93	2.51	2.894 (3)	105

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W1⋯O2	0.83 (5)	1.96 (5)	2.774 (3)	170 (4)
O1W—H2W1⋯O1i	0.94 (4)	1.99 (4)	2.906 (3)	167 (3)
C1—H1A⋯O1ii	0.93	2.55	3.424 (3)	157
C2—H2A⋯O1iii	0.93	2.54	3.382 (4)	150
C4—H4A⋯O1W	0.93	2.35	3.222 (4)	157
C6—H6A⋯O3iv	0.93	2.53	3.456 (4)	176
C9—H9A⋯O2	0.93	2.49	3.376 (3)	158
C13—H13A⋯O3iv	0.93	2.49	3.390 (4)	164
C14—H14B⋯O1ii	0.96	2.56	3.479 (4)	161

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .